JEE (Main) / Chemistry / RPP-08

Isomerism and Hydrocarbon: RPP-08

Single Correct Questions

1. Which of the following compounds exhibits stereoisomerism? [JEE (Main) 2002]
(1) 2 - Methyl butene (2) 3 - Methyl butyne
(3) 3 - Methyl butanoic acid (4) 2 - Methyl butanoic acid

1
CH3
H H
3
2. 2
H H
CH3
C2 is rotated anticlockwise by 120° about C2−C3 bond. The resulting conformer is [JEE (Main) 2004]
(1) partially eclipsed (2) eclipsed (3) gauche (4) staggered

3. In the following reaction sequence, structures of A and B, respectively will be : [JEE (Main) 2020]

HBr Na
 A Ether (intramolecular Product) B
CH2Br
OH OH Br CH2Br

Br OH
(1) & (2) &
CH2Br CH2Br O

Br Br OH OH

OH Br
(3) & (4) &
O
CH2Br CH2Br

4. 1-methyl ethylene oxide when treated with an excess of HBr produces : [JEE (Main) 2020]
Br Br
(1) (2)
CH3 Br
Br
CH3 Br
(3) Br (4)
CH3

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5. The major product in the following reaction is: [JEE (Main) 2020]
O

+ H3O
CH3

O O

(1) (2)
OH CH3 CH3

OH OH O

(3) (4) OH
CH3 CH3

6. The major product of the following reaction is : [JEE (Main) 2020]

H3C OH dil. H2SO4

H3C H3C
CH3
H3C OH
(1) (2)
H3C OH CH3 OH
OH
H3C CH3

CH3
H3C OH OH
(3) (4)
H3C HO CH3
OH
H3C CH3

7. Which of the following reactions will not produce a racemic product ? [JEE (Main) 2020]
CH3 O
HCl HCN
(1) CH3–C–CH=CH2 (2) CH3–C–CH2CH3
H

O
HCN HBr
(3) CH3–C–CH2CH3 (4) CH3CH2CH=CH2

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CH3 C
8. What is the major product formed by HI on reaction with C CH2 ? [JEE (Main) 2021]
CH3
CH3
CH3 CH3

(1) CH3 C CH CH2I (2) CH3 C CH CH3

CH3 H CH3 I

CH3

(3) CH3 C CH CH3 (4) CH3 CH CH CH2 CH3

I CH3 CH3 I

9. Identify products A and B : [JEE (Main) 2021]

CH3
dil. KMnO4 CrO3
273 K
A B

CH3 CH3 CH3 CH3

(1) A : OH B: (2) A : OH B: OH
OH O OH O

O CH3 CH3
(3) A : OHC–CH2CH2CH2–C–CH3 (4) A : B:
O OH O
B : HOOC–CH2CH2CH2–C–CH3

10. Identify A in the given chemical reaction. [JEE (Main) 2021]

CH3
CH2
CH3 Mo2O3
773 K, 10-20 atm
'A'
CH2 CH major product
CH2 CH3

(1) (2)

CH3 CH3
(3) (4)

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11. The major product of the following reaction is: [JEE (Main) 2021]
NO2

H2SO4

NO2 NO2

(1) (2)

NO2
NO2
(3) (4)

12. The major product of the following reaction is: [JEE (Main) 2021]
H2 /CO
CH3CH2CH = CH2 ⎯⎯⎯⎯
Rh catalyst
→
(1) CH3CH2CH=CH–CHO (2) CH3CH2C CH2
|
CH3
(3) CH3CH2CH2CH2CHO (4) CH3CH2CH2CHO

13. For the given reaction : [JEE (Main) 2021]

HC CHBr A
|
CH3 (major product)
H3C CH3
(1) CH3CH2CH2NH2 (2) CH CH—NH2 (3) (4)
|
CH3
CH3

14. For the given reaction :

CH2CH3
Br2
⎯⎯⎯
UV light
→ 'A'
(major product )
monobrominated
CN
What is 'A'? [JEE (Main) 2021]
H2N
CH2CH3
Br
(1) (2) CN
CN Br
Br CH3
CH CH2CH3

(3) (4)

CN Br CN

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15. Given below are two statements :

Statement I : C2H5OH and AgCN both can generate nucleophile.
Statement II : KCN and AgCN both will generate nitrile nucleophile with all reaction conditions.
Choose the most appropriate option : [JEE (Main) 2021]
(1) Statement I is true but statement II is false
(2) Both statement I and statement II are true
(3) Statement I is false but statement II is true
(4) Both statement I and statement II are false

16. Assertion A : Enol form of acetone [CH3COCH3] exists in < 0.1% quantity. However, the enol form of
acetyl acetone [CH3COCH2OCCH3] exists in approximately 15% quantity.
Reason R : enol form of acetyl acetone is stabilized by intramolecular hydrogen bonding, which is not
possible in enol form of acetone.
Choose the correct statement : [JEE (Main) 2021]
(1) A is false but R is true
(2) Both A and R are true and R is the correct explanation of A
(3) Both A and R are true but R is not the correct explanation of A
(4) A is true but R is false

17. Compound with molecular formula C3H6O can show : [JEE (Main) 2021]
(1) Positional isomerism
(2) Both positional isomerism and metamerism
(3) Metamerism
(4) Functional group isomerism

18. Which one of the following pairs of isomers is an example of metamerism ? [JEE (Main) 2021]
O
CH3
C6H5 and H5C6 H
(1) CH3CH2CH2CH2CH3 and H3C–C–CH3 (2)
CH3 O
OH
O O
OH and H5C6
(3) H5C6 (4) and

19. Which of the following molecules does not show stereo isomerism ? [JEE (Main) 2021]
(1) 3,4-Dimethylhex-3-ene
(2) 3-Methylhex-1-ene
(3) 3-Ethylhex-3-ene
(4) 4-Methylhex-1-ene

20. Staggered and eclipsed conformers of ethane are : [JEE (Main) 2021]
(1) Polymers (2) Rotamers (3) Enantiomers (4) Mirror images

21. The number of stereoisomers possible for 1,2-dimethyl cyclopropane is : [JEE (Main) 2021]
(1) One (2) Four (3) Two (4) Three

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22. Arrange the following conformational isomers of n-butane in order of their increasing potential
energy : [JEE (Main) 2021]
CH3 CH3 CH3 H
H H CH3 H CH3 H

H
H CH3 H H H H H H H H H3C CH3H
I II III IV
(1) II < III < IV < I (2) I < IV < III < II (3) II < IV < III < I (4) I < III < IV < II

23. In the following structures, which one is having staggered conformation with maximum dihedral
angle? [JEE (Main) 2022]
CH3 CH3
CH3 CH3
H CH3 H H H CH3
(1) (2) (3) (4)

H H H H
H H H H
H H CH3 CH3 H H

Integer type question

24. The number of chiral carbons in chloramphenicol is _______ . [JEE (Main) 2020]

25. In the following sequence of reactions the maximum number of atoms present in molecule 'C' in one
plane is _________.
A ⎯⎯⎯ → B ⎯⎯⎯⎯⎯
Redhot CH Cl(1.eq.)
Cu tube
3
Anhydrous AlCl3
→C [JEE (Main) 2020]
(A is a lowest molecular weight alkyne)

26. Consider the following chemical reaction.

CH  CH ⎯⎯⎯⎯⎯⎯⎯⎯
(1) Red hot Fe tube,873 K
(2) CO,HCl , AlCl3
→ Product
The number of sp2 hybridized carbon atom(s) present in the product is _______. [JEE (Main) 2021]

27. The number of acyclic structural isomers (including geometrical isomers) for pentene are ____
[JEE (Main) 2021]

28. The dihedral angle in staggered form of Newman projection of 1, 1, 1-Trichloro ethane is ......... degree.
(Round off to the nearest integer) [JEE (Main) 2021]

29. Observe structures of the following compounds

NH2
Cl
OH OH
H2N
O O OH

The total number of structures/compounds which possess asymmetric carbon atoms is __________.
[JEE (Main) 2022]

30. The number of chiral alcohol(s) with molecular formula C4H10O is______. [JEE (Main) 2022]

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Answer Key

Question 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Answer 4 3 4 4 2 2 1 3 2 4 3 3 4 3 1
Question 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Answer 2 4 4 3 2 4 4 3 2 13 7 6 60 3 1

Solutions
1. Ans. (4)
H
|
*
CH3—CH2—C—COOH : Has a chiral carbon, optically active.
|
CH3
2-methyl butanoic acid

2. Ans. (3)
1
CH3 H
H H H H
3 120° 3
2 Anti-clockwise 2
1
H H H3C H
CH3 CH3
gauche

3. Ans. (4)
O OH OH

HBr Br Na/ether

CH2–Br CH2–Br

4. Ans. (4)
Br
HBr (1)Br–
CH3–CH–CH2 CH3–CH–CH2 CH3–CH–CH2
(2) HBr
O O
 Br
H

5. Ans. (2)
••
O OH
••

H+


CH3 CH3
(Aromatic stable product)

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6. Ans. (2)
H3C CH3

+ H3C
H3C OH H
dil.H2SO4
H3C 

H2O

+
–H

OH2
OH

7. Ans. (1)
CH3 CH3 CH3
⊝
 H–shift
CH3–CH–CH=CH2 + H—Cl CH3–CH–CH–CH3 CH3–C–CH2–CH3

⊝
Cl

CH3
CH3–C–CH2–CH2
Cl
(No chiral centre, so no racemisation possible)
8. Ans. (3)
I
 1,2 shifting 
H–I of Me– I–
Electrophilic
addition

9. Ans. (2)
HO O
dil.KMnO4 CrO3
273 K

OH OH
(A)
10. Ans. (4)
1
2 6
Mo2O3 + 4H2
3 5 773 K, 10-20 atm
4
Mo2O3 at 773 K temperature and 10-20-atm pressure is aromatising agent.

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11. Ans. (3)

NO2 NO2 NO2
H2SO4


Major Minor

Hyperconjugation dominate over inductive


+
NO2 NO2

12. Ans. (3)

OXO PROCESS (Hydroformylation) :
CH3 − CH2 − CH = CH2 + CO + H2 ⎯⎯⎯Rh
catalyst
→
+
CHO (Major)

13. Ans. (4)

H3C CH3
CH=CHBr CCH
| |
CH3 CH3
CH3

14. Ans. (3)

Br
|
CH2—CH3 CH—CH3
Br2
UV light

CN CN

15. Ans. (1)

16. Ans. (2)

CH3–C–CH3 CH2=C–CH3
|| |
O OH
(Keto form) (enol form)
enol from of acetone is very less (< 0.1 %)
H-bonding
H O
O
CH3–C–CH2–C–CH3 CH3–C C
CH3
CH
O O
enol from (more than 50%)

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17. Ans. (4)

C3H6O  CH3–CH2–CH=O
& CH3–C–CH3
O
They are functional group isomerism.

18. Ans. (4)

O

O
are metamers.

19. Ans. (3)

3-Ethylhex-3-ene will not show stereo isomerism it's diagram is.
(1) Not show
geometrical
isomerism
(2) Not show
optical
isomerism

20. Ans. (2)

Staggered and eclipsed conformers of ethane also known as rotamers

21. Ans. (4)

+ +

A B C

22. Ans. (4)

More stable less potential energy.
Stability order : I > III > IV > II
So
Potential energy : II > IV > III > I

23. Ans. (3)

Dihedral angle : It’s the angle b/w 2 specified groups (–CH3 here)
Staggered form is Given in option (C) & the angle is 180°

24. Ans. (2)

OH OH
*
* Cl
O
N NH CH
O C Cl
||
O
Chloramphenicol

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25. Ans. (13)

Red Hot
(H—C C—H) Cu-tube
(A)
Lowest m.wt. alkyne
CH3—Cl(leq)
Anhydrous AlCl3

H
H
C
H

Total 13 atom are present in same plane (7 carbon & 6 hydrogen atoms. )

26. Ans. (7)

O
||
C—H

Red hot CO + HCl

3CHCH Fe tube
AlCl3

In benzaldehyde total number of sp2 'C' are 7.

27. Ans. (6)

(trans)

(cis)

28. Ans. (60)

1,1,1–Trichloro ethane [CCl3–CH3]
Cl
H H

Cl Cl

H
Dihedral angle() = 60°
(staggered form)

29. Ans. (3)

Cl NH2 *
OH
* * *
O * OH

Number of compounds containing asymmetric carbons are three.

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30. Ans. (1)

CH3 – CH2 –CH2–CH2 – OH

CH3—CH—CH2—CH3
|
OH
CH3
|
CH3—CH—CH2—OH
CH3
|
CH3—C—CH3
|
OH
Out of which only two are chiral

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